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Side Hustle Series: Stacy Pollack

Samantha Lloyd on August 2, 2019
stacy pollack writer career coach

The side hustle series is a new initiative on Hover that highlights the hardworking folks who operate businesses on the side of their day job. In our inaugural piece, we highlight Stacy Pollack, a writer and career coach.

Meet Stacy Pollack

Hey! My name is Stacy Pollack and I am a Learning and Development specialist. I create programs for corporate groups that help them build skills and develop their careers.

When I’m not at work, I’m writing my blogs for the website Glassdoor. I run my website, which is my new website (and a work in progress!) My goal is to eventually build up my own blog, on top of the writing I do for other websites. 

I write about my thoughts and experiences on career development, personal growth, and human resources. My work has been republished on major publications like NBC News, Motley Fool, Fast Company, Thrive Global, and more! I’ve also contributed several chapters to various books on networking and career building.

Why did you start this side hustle – what inspired you?

When starting my career, there were so many things I didn’t understand about how things worked in the professional world. Office politics, networking, professional etiquette, beating the ATS system, managing negotiations, etc. Having spent the majority of the first two years after university job hopping and job searching, I quickly learned so much about all these things. 

I also started to build my expertise in the field of Human Resources, and went back for my masters in Educational Technology. I wanted to start sharing my experiences both as a job seeker, as well as a human resource professional with people in the hopes that I could help people in the way I needed to be helped and guided early on. 

This led me to my first side gig, writing resumes and cover letters for people (which I still do today)! This has been a total word of mouth business, but a service I realize so many people need. 

What keeps you motivated to keep working after your 9-5?

My passion and drive for the work! I love helping people put their best foot forward at work and learn ways they can self improve. I’m starting to realize what a large reach writing for Glassdoor has given me, and feel humbled at how many people have reached out from across the world to let me know that an article I had written helped them find success in certain situations.

How do you schedule your time so that you can balance a full-time job and a side hustle?

To-do lists! I use a tool called “air table” to help me keep track of my big goals and keep me organized. Tools that block social media and apps both on my phone and desktop are game changer

What is your favourite and least favourite thing about your side hustle?

More financial flexibility, a creative outlet, and the way it is helping me build my brand are definitely positives. On the other side, diminished energy and focus! I love my side hustle, but it can be really hard to prioritize it. It takes a lot of discipline and focus to make things happen, especially when you’ve been working from 9:00-5:00

What advice would you give to anyone looking to pursue a similar path?

Start small, and take note of the compounding effect that your work can have! When I think about what I want to do with my side business in comparison to what I have done now, I get discouraged. But when I look at everything I have accomplished over the year, two years, three years, it helps motivate me and push me forward. 

It takes time to build side-hustling habits into your routine so be patient and kind with yourself on that too. It’s not easy to say no to plans and stay in when it’s sunny outside, but the sacrifice is important when trying to get something off the ground. It’s also equally important to know when it’s time to rest, recharge, and say no to working! 

What do you do to step away from working and relax?

I try and never bring my laptop into bed and stop working by 9:30pm latest to make sure I always get a good sleep. That is really what fuels me most. I also love a nice bubble bath to help me relax from the day. Beyond that, cooking with friends is my favorite way to detach from work.

What about Hover do you like for managing your side hustle domain name?

It was super easy to set my domain name up at! I connected my Hover domain to my SquareSpace website in no time at all.

What is it about writing that you love?

Hmm…I love the creativity, and I love watching articles being shared. It’s a huge thrill when I see my articles on major business publications like NASDAQ, Motley Fool, and even NBC News. It helps me alleviate some of the imposter syndrome I battle with about being in the business world, and sometimes I still can’t believe that people are interested in reading my work! 

People struggle so much with finding meaningful work, and doing well in their jobs. I feel privileged to have a platform that allows me to connect with so many people and share advice and insights that could potentially help them, both as employers and employees. 

How did you get started in writing?

In one of my first jobs, I went through an experience where I had to negotiate, and fight tooth and nail for a promotion. My senior manager had quit, and I was doing her workload for over a year, while getting paid as a coordinator. After much protest, and successfully advocating for myself, I was able to get my promotion and proper compensation for the work I was doing. I thought to myself, “Hey, this is something people need to learn how to do, and I should share this life experience in case others are going through similar challenges”. 

So I wrote a blog post about it called “Get the promotion you deserve in 2018”, sent it into Glassdoor, and have been a contributing writer for their blog ever since! 

What has been a big lesson in running your own side hustle in writing?

You can’t do it all in one day! Writing out your goals, both short term and long term is really helpful in being able to see your own growth and keep you on the ball. My biggest lesson has been to celebrate my small steps, and be realistic about what I can accomplish in 24 hours. It can feel discouraging when I look at my big goals and realize how much I have left to do, but reflecting on all the success of each little step I take and seeing those compound effects helps push me forward and gives me motivation to keep chipping away at my bigger life goals. 

Show us your favourite content pieces you’ve written! Which ones have had the biggest impact on your audience?

I recently wrote a piece about what it means to be a working mom in 2019. I got to speak with so many inspiring women about the challenges, successes, and work left to be done around equality. Each of their stories really resonated with me for different reasons. The article was published by NASDAQ.

It made me so happy to know that such an important topic was getting such a broad reach, and hopefully influencing organizations to make changes in ways that can help working parents all over the world. 

Another piece I loved writing was called “How to Find a Side Job”, and it was featured in Thrive Global. This piece was really special to me because I got to collaborate with Dorie Clark, a writer who has completely changed the way I think about my life and work. Her book “Entrepreneurial You” inspired me to kick my freelance business into action, so when she agreed to collaborate with me on this article, I felt completely star struck. I could not believe someone like her would agree to speak with someone like me!

What’s a go-to technique or tool you use to manage your writing?

Google Docs are key! I keep a running doc of all my article ideas and topics, and when I start a new article, I create it first in Docs. This way, when i get a burst of inspiration or an idea, I can have whatever article I’m working on open on the fly. 

I also leverage Facebook and LinkedIn a lot when I am asking questions to get research or source people to interview. I use Toggl to manage my time and make sure I’m not spending too much time on each article. Otherwise I could sit and edit it for hours.